Diisopropyl Ether → Cefditorin pivoxil

HRID 2373532Notes

Reaction equation

HRID 2373532 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]\[C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([O-:33])=[O:32].[Na+].C(=O)(O)[O-].[Na+].[C:40]([O:46][CH2:47]I)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].C(OC(C)C)(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.CN(C=O)C>[CH3:1][C:2]1[N:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]\[C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([O:33][CH2:47][O:46][C:40]([C:41]([CH3:44])([CH3:43])[CH3:42])=[O:45])=[O:32]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 236730425-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-, sodium salt (1:1), (6R,7R)-

Product 1

HCID 6437877Cefditorin pivoxilYield 97%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To DMF (80 ml), Cefditoren Sodium (10 gm) was added at 30° C. and stirred to get a clear solution. To the clear solution, solid sodium bicarbonate (1.6 gm), and tetra butyl ammonium hydrogen sulphate were added. The reaction mass was cooled to −20° C. and iodomethyl pivalate (9.76 gm) was charged and stirred for 60 minutes. The reaction mass was poured into isopropyl ether (100 ml). To this reaction mixture DM Water (100 ml) was added. The solid obtained was stirred at 5° C., filtered, washed with water and IPE, and finally dried to get the title compound. Purity(HPLC): 97-99% Yield: 8.5 gm.

Workup

  1. customto get a clear solution
  2. stirringstirred for 60 minutes
  3. customThe solid obtained
  4. stirringwas stirred at 5° C.
  5. filtrationfiltered
  6. washwashed with water and IPE
  7. customfinally dried

Sources & evidence

ORD record
ord-aaa7e59a933d4814aef17dc9c80dc9f7
Source dataset
uspto-grants-2008_12
Patent number
US07459550B2

Reaction notes

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